LOWER RIM p-TERT-BUTYLCALIX[4]ARENE DERIVATIVES CONTAINING GALACTITOL PENDANTS: COMPLEXATION OF 5,11,17,23-TETRAKIS-(1,1-DIMETHYLETHYL)-25,27-DIHYDROXY -26,28-BIS-2-N-(1-DEOXY-D-GALACTITYL)-AMINOETHOXYCALIX[4]ARENE WITH Pb(II) AND F(-I)
Reductive amination of D-galactose with the bisubstituted p-tert-butylcalix[4]arylethylamine in the presence of sodium cyanoborohydride allowed the introduction of one or two galactitol residues as pendants on the lower rim. The bisubstituted secondary amine, 5,11,17,23-tetrakis-(1,1-dimethylethyl)-...
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| Autores principales: | , , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2004
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072004000400002 |
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| Sumario: | Reductive amination of D-galactose with the bisubstituted p-tert-butylcalix[4]arylethylamine in the presence of sodium cyanoborohydride allowed the introduction of one or two galactitol residues as pendants on the lower rim. The bisubstituted secondary amine, 5,11,17,23-tetrakis-(1,1-dimethylethyl)-25,27-dihydroxy-26,28-bis-2-N-(1-deoxy-D-galactityl)-aminoethoxycalix[4]arene (III) was obtained in 24.1% yield. Complexation of this compound with Pb (II) and F(-I) was studied by ¹H-NMR and spectrophotometric titration in acetonitrile, showing a stoichiometry of 1:2 (ligand:ion) with equilibrium constants of log K1=2.22 ± 0.08 and log K2=2.07 ± 0.07 for Pb(II), and log K1=1.21 ± 0.05 and log K2=1,17 ± 0.04 for F (-I) ion |
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